Holiday rentals in Kailua

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Popular amenities for Kailua holiday rentals

Other great holiday rentals in Kailua

Flat in Hauula
4.6 out of 5 average rating, 138 reviews

Second Wind, Ocean front, Sunrise View!

MeredithRating, 5 stars2 weeks ago
This place was fantastic! So happy we chose to stay here. Beautiful view from the living room. The beach is so peaceful. I loved that there was a pool and a gym. The gym is right on the beach and has what I needed for lifting weights. It was the best. This beach is great for sunrises and early mornings. The kitchen was great. Only thing missing was a baking pan for the oven, maybe I just couldn’t find it. There were appliances and cooking utensils and the glassware and plates were cute. We also enjoyed the lanai. I highly recommend this place. One of the best Airbnb locations we have ever stayed in.
Guest suite in Kailua
5 out of 5 average rating, 15 reviews

Lanikai Garden Studio - Licensed Since 1985!

JohnRating, 5 stars40 months ago
Even better than we expected! (And we expected it to be great). The studio is larger than we thought and every detail is carefully thought out. The place is extremely clean and very close to the beach. Do not worry about privacy, the studio has its own gate and garden area. We hope to return soon.
Guest house in Kailua
4.79 out of 5 average rating, 179 reviews

Absolutely Oceanfront-60'Waterfall Pool-Legal

GinaRating, 5 stars2 months ago
Thomas’ rental was an amazing private retreat for me. The ocean front location is spectacular. Waking up to the sunrise, going to sleep with the tradewinds and crashing waves. It’s on a lava beach so it’s rocky but I discovered a swimmable beach 13 houses down where green turtles sometimes swim beside you. Gorgeous scenery and a peaceful, private location. The interior was immaculate and well cared for. After going to Whole Foods prior to my arrival, I didn’t leave the premises except to head down to the beaches!!! Highly recommend. I hope to spend a longer time there next time I’m back in Oahu.
Superhost
Apartment in Waikiki
5 out of 5 average rating, 3 reviews

Majestic Studio Heart of Waikiki Free Parking

JonathanRating, 5 stars1 week ago
This condo provided my wife and I with a prime location near the ocean and walking distance from so many restaurants. Instead of paying hefty resort and parking fees (condo comes with parking), we opted for this condo and very glad we did. We spent a lot of our time exploring the island so we were gone most of the day but the times we needed to rest, it was nice having so many great options just a few minutes walk. The host was very accommodating and very responsive. Definitely recommend staying here for any body who plans to do more than just stay at the resort. And if you just want to hang in Waikiki the entire time, you’re also just a 5 min walk from the ocean where all the action is. Either way can’t go wrong with Anton’s place. Mahalo!
Guest favourite
Cottage in North Shore
4.88 out of 5 average rating, 119 reviews

Best Kept Secret on Oahu! and WE ARE LICENSED!!!

SusannaRating, 5 stars4 weeks ago
We greatly enjoyed our time in his house. We had fantastic sunsets on the lanai. It was very relaxing to spent the afternoon on the lanai and to watch and hear the sea. You can easily reach a small beach from the house, which we only did for some late afternoon walks. We went snorkeling at Shark‘s Cove and at Waimea Beach, we could see a lot of fishes and turtles, inside and outside of the water. The location of the house was very good for us, you can easily reach different beaches, go on a sea shore hike or visit Pearl Harbour. The house was ideal for the two of us. We wanted to relax at the sea and do a lot of snorkeling and swimming which we could do every day. Peter was very friendly and helpful.
Guest suite in Hauula
5 out of 5 average rating, 18 reviews

Hauula Beach Living with Aloha

ElizabethRating, 5 starstoday
Lovely apartment with all the amenities you could want for a delightful stay on the Windward side of Oahu. Great deck on a river, too!
Tiny home in Kailua
5 out of 5 average rating, 3 reviews

Affordable Hawaii Camping Trip | Gear Included

ElizabethRating, 5 stars1 week ago
Was such an affordable and amazing way to spend our time in oahu! We are first time van campers and this trip seriously sparked something in us, a love and respect for the outdoors & even more for our Polynesian islands which we hold so dear. Mahalo family 🤍🤍
Superhost
Townhouse in North Shore
4.95 out of 5 average rating, 21 reviews

Sunset Hale

AngelaRating, 5 stars3 weeks ago
Our family of four ( including a 3 & 5 y/o) had a wonderful stay! The home had everything we needed and the location was amazing! A great reef to snorkel right out front of the unit while the kiddos rested. Our favorite beaches were less than a 5 minutes drive west of the unit and had no tourists, lots of trees for shade and opportunities to snorkel with turtles. Would highly recommend for those wanting a more quiet vacation spot.

Quick stats about holiday rentals in Kailua

  • Total rentals

    360 properties

  • Total number of reviews

    11K reviews

  • Family-friendly rentals

    200 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    90 properties have a pool

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

Destinations to explore

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  5. Kailua